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1.
Fitoterapia ; 157: 105133, 2022 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-35114336

RESUMO

Six diterpenoids including three ent-kauranes (1-2, 4) and three cleistanthanes (3, 5-6) were isolated from the roots and stems of Phyllanthus acidus (L.) Skeels. Of them, (16S)-ent-16,17,18-tri-hydroxy-19-nor-kaur-4-en-3-one (1), phyllanthone A (2), and 6-hydroxycleistanthol (3) are new compounds, while the ent-kaurane diterpenoids were reported from the titled plant for the first time. Their structures were elucidated on the basis of the extensive spectroscopic analyses. Compounds 2 and 4-6 displayed cytotoxic potential with IC50 values ranging from 1.96 to 29.15 µM. They also showed moderate anti-inflammatory activities (IC50 = 6.30-12.05 µM). Particularly, the new ent-kaurane 2 displayed cytotoxic potential against HL-60 (IC50 = 2.00 µM) and MCF-7 (IC50 = 3.55 µM) cells, and anti-inflammatory activity (IC50 = 6.47 µM).


Assuntos
Diterpenos do Tipo Caurano/toxicidade , Diterpenos/toxicidade , Phyllanthus/química , Extratos Vegetais/toxicidade , Alcaloides/química , Alcaloides/isolamento & purificação , Alcaloides/toxicidade , Linhagem Celular Tumoral , Diterpenos/química , Diterpenos do Tipo Caurano/química , Humanos , Concentração Inibidora 50 , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Extratos Vegetais/síntese química , Raízes de Plantas/química , Caules de Planta/química
2.
Bioorg Chem ; 114: 105125, 2021 09.
Artigo em Inglês | MEDLINE | ID: mdl-34217976

RESUMO

The young leaves of Phyllanthus acidus (Euphorbiaceae) are commonly used as edible vegetables in Indonesia, Thailand, and India, and their water infusions as dieting aids for people trying to remain slim. However, it is regarded as a poisonous plant in Malaya, and current researches are insufficient to provide a conclusion on its toxicity and safety under large doses. In this study, we firstly found that the refined nonpolar extracts of P. acidus leaves showed significant cytotoxic effect against BEAS-2B and L02 normal cell lines with IC50 values of 2.15 and 1.64 mg/mL, respectively. Further bioactivity-guided isolation produced four new rare dichapetalins (pacidusins A-D) from the most active fraction. Their structures including absolute configurations were elucidated by extensive spectroscopic data and X-ray diffraction analysis. All the isolated dichapetalins exhibited moderate cytotoxicity against, BEAS-2B and L02 normal cell lines with IC50 values ranging from 12.44 to 22.55 µM, as well as five human cancer cell lines with IC50 values ranging from 3.38 to 22.38 µM. Furthermore, the content of the main dichapetalins in the leaves were determined by analytical HPLC, which showed that the leaves contained a very high amount of the four isolated dichapetalins with a total yield of 0.488 mg/g of dry plant material. These toxic dichapetalins may lead to adverse health effects in higher doses. Our findings indicate that the dichapetalin containing leaves may not be suitable for consumption in large quantities as food, but demonstrate their potency as anti-cancer agents for new drug discovery.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Phyllanthus/química , Extratos Vegetais/farmacologia , Folhas de Planta/química , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Relação Estrutura-Atividade
3.
Nat Prod Bioprospect ; 11(5): 565-572, 2021 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-34114172

RESUMO

The extensive chemical investigation on the branches and leaves of Terminalia chebula var. tomentella (Combretaceae) led to the isolation of two new lignan glucosides with a furofuran skeleton, termitomenins F (1) and G (2). In addition, 19 known compounds including five lignan glucosides (3-7), six hydrolyzable tannins (8-13) and eight simple phenolics (14-21) were also identified. Their structures were determined by comprehensive spectroscopic analyses. It is noted that 8 and 9 were C-glycosidic hydrolyzable tannins with one hexahydroxydiphenoyl and one gallagyl group linked to an open-chain glucosyl C-1/O-2/O-3 and O-4/O-6, respectively, which were rarely found in plants. Nine known compounds, 6-9, 13, and 18-21, were procured from the titled plant for the first time, while 3-5, 10-12 and 14-17 were also found in the fruits. Notably, the known hydrolyzable tannins 8-13 exhibited stronger α-glucosidase inhibitory activities with IC50 values ranging from 0.10 to 3.12 µM, than the positive control, quercetin (IC50 = 9.38 ± 0.33 µM).

4.
Nat Prod Res ; : 1-6, 2021 Jun 02.
Artigo em Inglês | MEDLINE | ID: mdl-34074201

RESUMO

Phyllaciduloids E (1) and F (2), two new cleistanthane diterpenoids, were isolated from the leaves of Phyllanthus acidus (L.) Skeels (Phyllanthaceae). Their planar structures were established by spectroscopic analysis and comparison with literature values. The relative configurations of phyllaciduloids E and F were confirmed by DFT-NMR chemical shift calculations and subsequent CP3 probability methods. Phyllaciduloids E and F were evaluated for their cytotoxicity. However, no significant activities were detected at concentrations up to 40 µM.

5.
J Ethnopharmacol ; 275: 114135, 2021 Jul 15.
Artigo em Inglês | MEDLINE | ID: mdl-33892063

RESUMO

ETHNOPHARMACOLOGICAL RELEVANCE: Terminalia chebula (TC), a well-known Indian Ayurvedic medicine introduced into China in the Sui and Tang Dynasties, has been recorded and used medicinally as Fructus Chebulae, together with its variety tomentella (TCT) in the Chinese Pharmacopoeia. They have been also used commonly for the treatment of diabetes mellitus by Tibetan medicine. AIM OF THE STUDY: To investigate the main bioactive and therapeutic principles in the fruits of TCT, based on the extensive evaluation of their anti-inflammatory and hypoglycemic activities. MATERIALS AND METHODS: The TCT fresh fruits were analyzed by HPLC and separated further by column chromatography and preparative HPLC. The isolated compounds were identified by extensive spectroscopic analyses, including 1D/2D NMR, MS, UV, IR and ECD. Anti-inflammatory activity was evaluated by inhibition of NO production in RAW264.7 cells. The specific iNOS (PDB ID: 3E7G) structure was prepared by Discovery Studio 4.0, and the molecular docking simulation was performed on GOLD (version 5.2.2). Hypoglycemic activity was measured using the substrate solution of 4-nitrophenyl-α-d-glucopyranoside enzyme and buffer solution. RESULTS: The HPLC analysis method of polyphenols in the fruits of TCT was established, and 13 main chromatographic peaks were identified, including six hydrolyzable tannins (2, 4-7, 10-11), three simple phenols (12-14), and one oleanane pentacyclic triterpene, arjungenin. Extensive chromatographic separation of TCT fresh fruits yielded 14 compounds, including one new natural hydrolyzable tannin, 2,3-(S)-HHDP-6-O-galloyl-d-glucose (1). The known compounds were identified as 10 hydrolyzable tannins (2-11) and three simple phenols (12-14). Compounds 10 (IC50 = 36.43 ± 0.21 µM), 11 (IC50 = 42.28 ± 0.09 µM) displayed stronger NO inhibitory activity than the positive control L-NMMA (IC50 = 42.34 ± 0.66 µM), while 2, 4, and 9 showed moderate inhibitory activity against NO production. Further molecular docking simulation of specific iNOS on 10 and 11, as well as five previously isolated lignans 15-19 showed that there were no obvious rules between docking results and the in vitro NO inhibitory activity for hydrolyzable tannins (10 and 11), while the mechanism of anti-inflammatory activity for lignans was related to the substitution of conjugated aldehyde groups. Moreover, most of the hydrolyzable tannins (1-2, 4-5, 9-11) and simple phenol (12) displayed stronger inhibitory effects on α-glucosidase than the positive control, quercetin (IC50 = 6.118 ± 0.071 µM), with IC50 values ranging from 0.079 to 16.494 µM. Among these bioactive isolates, the hydrolyzable tannins 2, 4-5, and 9-11, and simple phenol 12 are major chemical components in TCT fruit. CONCLUSIONS: The results showed that lignans and hydrolyzed tannins are the main active ingredients of TCT fruits, responsible for the traditional treatment of sore throat and cough. Moreover, hydrolyzed tannins and simple phenolic compounds with potential hypoglycemic activity are closely related to the ethno-pharmacological uses of TCT fruits on diabetes in Tibetan medicine.


Assuntos
Anti-Inflamatórios/farmacologia , Hipoglicemiantes/farmacologia , Fenóis/farmacologia , Extratos Vegetais/farmacologia , Terminalia/química , Animais , Anti-Inflamatórios/análise , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Frutas/química , Inibidores de Glicosídeo Hidrolases/farmacologia , Taninos Hidrolisáveis/análise , Taninos Hidrolisáveis/química , Taninos Hidrolisáveis/farmacologia , Hipoglicemiantes/análise , Hipoglicemiantes/química , Hipoglicemiantes/isolamento & purificação , Técnicas In Vitro , Lignanas/análise , Lignanas/química , Lignanas/farmacologia , Camundongos , Simulação de Acoplamento Molecular , Óxido Nítrico Sintase Tipo II/antagonistas & inibidores , Óxido Nítrico Sintase Tipo II/química , Fenóis/análise , Fenóis/química , Fenóis/isolamento & purificação , Extratos Vegetais/análise , Extratos Vegetais/química , Células RAW 264.7 , Triterpenos/análise , Triterpenos/química , Triterpenos/farmacologia , alfa-Glucosidases/metabolismo
6.
Phytochemistry ; 184: 112656, 2021 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-33524854

RESUMO

Three previously undescribed pyridyl-steroidal glycoalkaloids, solanindiosides A‒C, one rare 23S,26R-hydroxylated spirostanoid saponin, and two steroidal alkaloid aglycones, solanindins A and B, derived from the acid hydrolysis of solanindiosides A‒C, were isolated from the fruits of Solanum violaceum, together with five known analogues, including two rare steroidal glycosides, two lignans and a diterpene. Structurally, they comprise a 16ß-methoxy-23-deoxy-22,26-epimino-cholest-type skeleton moiety, and a 16ß-methoxy-3,23-dideoxy-22,26-epimino-cholest-3,5-dien derivative. The hitherto undescribed structures were established on the basis of extensive spectroscopic analyses. Configurations of sugar moieties were resolved by chemical derivations. Solanindiosides A‒C, (22R,23S,25R,26R)-spirost-5-ene-3ß,23,26-triol3-O-ß-d-xylopyranosyl-(1→3)-ß-d-glucopyranoside, solanindins A and B, and (1S,2S)-1-(4-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-[(2S,3R,4R)-tetrahydro-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)-2-furanyl]phenoxy]-1,3-propanediol were evaluated for their cytotoxic and antibacterial activities. (1S,2S)-1-(4-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-[(2S,3R,4R)-tetrahydro-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)-2-furanyl]phenoxy]-1,3-propanediol showed the most potent cytotoxic activity against MCF-7 cells (IC50 = 4.386 ± 0.098 µM), while solanindin B displayed some inhibitory effects against Staphylococcus aureus Rosenbach with MIC50 value of 37.32 ± 0.793 µM. In addition, (1S,2S)-1-(4-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-[(2S,3R,4R)-tetrahydro-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)-2-furanyl]phenoxy]-1,3-propanediol induced dose dependent apoptosis effect in MCF-7 cells.


Assuntos
Saponinas , Solanum , Frutas , Glicosídeos , Saponinas/farmacologia , Esteroides
7.
Nat Prod Res ; 35(21): 3540-3547, 2021 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-31979989

RESUMO

A novel highly oxygenated norbisabolane sesquiterpene, namely phyllanthacidoid U (1), along with nine known sesquiterpenes (2-10) was isolated from the roots and stems of Phyllanthus acidus (L.) Skeels (Phyllanthaceae), collected from Xishuangbanna, Yunnan province, China. Their structures were elucidated by means of extensive spectroscopic analysis and by comparison of their data with reported values in literatures. Instead of the C-13 ester O-glycosyl found mostly in the titled plant growing in Thailand, compound 1 possessed a rare N-ß-glucosamine-2-N-acetate moiety linked directly to the carbonyl at C-13 through an amido bond. Moreover, the acyl group at C-10 in 1 was (Z)-2-(2-hydroxyethyl)-pent-2-enedioyl group, instead of benzoic or p-hydroxybenzoic moieties found commonly in the reported norbisabolane sesquiterpenes. The known sesquiterpene 5 displayed stronger anti hepatitis B virus (HBV) activity with IC50 values of 1.69 ± 0.22 and 2.79 ± 0.69 µM towards HBV surface antigen (HBsAg) and HBV excreted antigen (HBeAg) secretion, respectively.


Assuntos
Phyllanthus , Sesquiterpenos , China , Antígenos E da Hepatite B , Vírus da Hepatite B , Estrutura Molecular , Extratos Vegetais
8.
Fitoterapia ; 148: 104793, 2021 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-33276011

RESUMO

Phytochemical investigation on the nonpolar extracts of P. acidus leaves afforded three new cleistanthane diterpenoids, named phyllanacidins A-C (1-3), in addition to three known ones (4-6). Among them, compounds 2 and 3 represent the first examples of 17-nor cleistanthane diterpenoids. Their structures including absolute configurations were elucidated on the basis of extensive spectroscopic data and single crystal X-ray diffraction analysis. All the isolated cleistanthane diterpenoids were evaluated for their cytotoxic activities against five human cancer cell lines. Compounds 4-6 exhibited moderate cytotoxicity with IC50 values ranging from 16.11 to 30.82 µM.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Diterpenos/farmacologia , Phyllanthus/química , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , China , Diterpenos/isolamento & purificação , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Folhas de Planta/química
9.
Plant Divers ; 42(5): 323-333, 2020 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-33134615

RESUMO

Panax notoginseng (Araliaceae) is an important ginseng herb with various health benefits and a history of cultivation in southwestern China over 400 years. In recent years P. notoginseng has faced serious continuous-cropping obstacles due to its large-scale cultivation. In this study, we aim to explore the allelochemicals of P. notoginseng and their interactions with various plants and rhizosphere microorganisms. The chemical constituents of the soil cultivated with 3-year-old P. notoginseng were studied by column chromatography, spectroscopic and GC-MS analyses. We identified 13 volatile components and isolated six triterpenes (1-4, 6-7) and one anthraquinone (5). Compounds 1-7 were tested for their effects on seed germination and root elongation in P. notoginseng, corn, wheat, turnip, water spinach and Arabidopsis thaliana. We also examined the effect of compounds 1-7 on the growth of ten rhizosphere microorganisms of P. notoginseng. At a concentration of 1.0 µg mL-1, compounds 3 and 5-7 caused the death of P. notoginseng root cells and compounds 2, 6 and 7 induced the death of root cells of A. thaliana. Compounds 1-5 and 7 inhibited elongation of A. thaliana root tip cells at a concentration of 10.0 µg mL-1. Moreover, at a concentration of 0.1 mg mL-1, compounds 3, 4, 6 and 7 inhibited the growth of probiotics and promoted the growth of pathogens of P. notoginseng. These results suggest that these isolated ursane-type triterpenoid acids and anthraquinone are potential allelochemicals that contribute to continuous-cropping obstacles of P. notoginseng.

10.
J Agric Food Chem ; 68(30): 7955-7963, 2020 Jul 29.
Artigo em Inglês | MEDLINE | ID: mdl-32628847

RESUMO

As a subgroup of flavoalkaloids, N-ethyl-2-pyrrolidinone substituted flavan-3-ols are reported to possess various biological activities that may play important roles in the beneficial healthcare functions of tea. The HPLC and LC-MS analyses showed the existence of N-ethyl-2-pyrrolidinone substituted flavan-3-ols in 'Jin-Ya', which is a Yunnan black tea produced only from the buds of the tea plant Camellia sinensis var. assamica. Further phytochemical study on this precious black tea led to the identification of 8 flavoalkaloids, 1-8, along with 11 known flavan-3-ols (9-14) and flavonol glycosides (15-19). The new compounds, (-)-6-(5″S)-N-ethyl-2-pyrrolidinone-epiafzelechin (1), (-)-8-(5″R)-N-ethyl-2-pyrrolidinone-epiafzelechin-3-O-gallate (2a), and (-)-8-(5″S)-N-ethyl-2-pyrrolidinone-epiafzelechin-3-O-gallate (2b), were identified based on extensive spectroscopic analysis. Flavoalkaloids 2-6 showed inhibitory activity on α-glucosidase with IC50 values ranging from 2.09 to 8.47 µM, compared to those of quercetin and acarbose (IC50 = 6.87 and 228.9 µM, respectively). Moreover, compounds 2, 3, and 6 displayed an inhibitory effect on acetyl-cholinesterase with IC50 values of 14.23, 33.79, and 34.82 µM, respectively, compared to tacrine (IC50 = 0.223 µM).


Assuntos
Alcaloides/química , Camellia sinensis/química , Inibidores Enzimáticos/química , Extratos Vegetais/química , Acetilcolinesterase/química , China , Glicosídeos/química , Humanos , Cinética , Estrutura Molecular , Folhas de Planta/química , alfa-Glucosidases/química
11.
J Ginseng Res ; 44(3): 405-412, 2020 May.
Artigo em Inglês | MEDLINE | ID: mdl-32372862

RESUMO

BACKGROUND: Root rot is a serious destructive disease of Panax notoginseng, a famous cultivated araliaceous herb called Sanqi or Tianqi in Southwest China. METHODS: The chemical substances of Sanqi rot roots were explored by chromatographic techniques. MS, 1D/2D-NMR, and single crystal X-ray diffraction were applied to determine the structures. Murine macrophage RAW264.7 and five human cancer cell lines were used separately for evaluating the antiinflammatory and cytotoxic activities. RESULTS AND CONCLUSION: Thirty dammarane-type triterpenes and saponins were isolated from the rot roots of P. notoginseng. Among them, seven triterpenes, namely, 20(S)-dammar-25-ene-24(S)-hydroperoxyl-3ß,6α,12ß,20-tetrol (1), 20(S)-dammar-3-oxo-23-ene-25-hydroperoxyl-6α,12ß,20-triol (2), 20(S)-dammar-12-oxo-23-ene-25-hydroperoxyl-3ß,6α,20-triol (3), 20(S)-dammar-3-oxo-23-ene-25-hydroperoxyl-12ß,20-diol (4), 20(S),24(R)-epoxy-3,4-seco-dammar-25-hydroxy-12-one-3-oic acid (5), 20(S),24(R)-epoxy-3,4-seco-dammar-25-hydroxy-12-one-3-oic acid methyl ester (6), and 6α-hydroxy-22,23,24,25,26,27-hexanordammar-3,12,20-trione (7), are new compounds. In addition, 12 known ones (12-16 and 19-25) were reported in Sanqi for the first time. The new Compound 1 showed comparable antiinflammatory activity on inhibition of NO production to the positive control, whereas the known compounds 9, 12, 13, and 16 displayed moderate cytotoxicities against five human cancer cell lines. The results will provide scientific basis for understanding the chemical constituents of Sanqi rot roots and new candidates for searching antiinflammatory and antitumor agents.

12.
J Agric Food Chem ; 68(17): 4865-4875, 2020 Apr 29.
Artigo em Inglês | MEDLINE | ID: mdl-32306731

RESUMO

Saponins of Panax notoginseng (Burk.) F.H. Chen have been classified as a type of composition in functional foods for numerous diseases. However, its mild effects and other characteristics limited clinical applications in diseases. Inspired by "nine steaming and nine processing" of P. notoginseng in traditional Chinese medicine, we developed a "steaming"-mimic protocol, which significantly changed the composition of saponins of P. notoginseng from the original, R1, Rg1, Re, Rb1, and Rd (raw-PNS), to the products after steaming, 20S/R-Rh1, Rk3, Rh4, 20S/R-Rg3, Rk1, and Rg5 (N-PNS). Surprisingly, N-PNS demonstrated promising activities in improving hyperlipidemia and reducing body weight and weight of white adipose tissue and the inhibition of adipogenesis in obese mice. In accordance with the results in vivo, N-PNS remarkably blunted adipogenesis at the early stage of differentiation dose-dependently in vitro. Moreover, we demonstrated that the activity may involve the adenosine monophosphate (AMP)-activated protein kinase (AMPK) signaling pathway by promoting phosphorylation of AMPKT172 and downregulating its downstream factors: sterol regulatory element binding protein 1c, stearoyl-CoA desaturase 1, and fatty acid synthase. Taken together, the steaming-induced eight compositions of saponins showed a very promising function in improving hyperlipidemia and obesity both in vivo and in vitro, providing fundamental evidence for future study and application in treatment of hyperlipidemia, obesity, and other lipid-related metabolic syndromes.


Assuntos
Medicamentos de Ervas Chinesas/administração & dosagem , Hiperlipidemias/tratamento farmacológico , Obesidade/tratamento farmacológico , Panax notoginseng/química , Saponinas/administração & dosagem , Proteínas Quinases Ativadas por AMP/genética , Proteínas Quinases Ativadas por AMP/metabolismo , Animais , Medicamentos de Ervas Chinesas/química , Humanos , Hiperlipidemias/genética , Hiperlipidemias/metabolismo , Masculino , Camundongos , Camundongos Endogâmicos C57BL , Obesidade/genética , Obesidade/metabolismo , Fitoterapia , Saponinas/química , Proteína de Ligação a Elemento Regulador de Esterol 1/genética
13.
Fitoterapia ; 143: 104571, 2020 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-32209392

RESUMO

An elaborated phytochemical study on the fresh fruits of Terminalia chebula var. tomentella (Combretaceae) led to the isolation of five new lignans, including three tetrahydrofuran (1-3) and two furofuran (4 and 5) derivatives, namely termitomenins A-E (1-5), along with 10 known ones. All of them were obtained from the titled plant for the first time. Their structures were determined by extensive spectroscopic analysis, including 1D/2D NMR, MS, UV, IR, electronic circular dichroism (ECD), time-dependent density functional theory (TDDFT) calculation of ECD spectra, and single crystal X-ray diffraction in case of 3. Compounds 1-15 exhibited certain anti-inflammatory activities. Interestingly, compounds 6 (IC50 = 18.17 ± 0.57  µM) and 7 (IC50 = 13.66 ± 0.38 µM) which contain an aldehyde group displayed stronger NO inhibitory activity than the positive control L-NMMA (IC50 = 42.34 ± 0.66 µM).


Assuntos
Anti-Inflamatórios/farmacologia , Lignanas/farmacologia , Terminalia/química , Animais , Anti-Inflamatórios/isolamento & purificação , China , Frutas/química , Furanos/isolamento & purificação , Furanos/farmacologia , Lignanas/isolamento & purificação , Camundongos , Estrutura Molecular , Óxido Nítrico/metabolismo , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Células RAW 264.7
14.
Nat Prod Res ; 34(10): 1373-1379, 2020 May.
Artigo em Inglês | MEDLINE | ID: mdl-30445878

RESUMO

The fresh leaves of Metapanax delavayi (Araliaceae) have been used as a common wild vegetable for salad and soup, and also herbal tea by the local people living in its growing areas of Yunnan province, China. Detailed chemical investigation led to the identification of a new triterpenoid saponin, 3-O-α-L-arabinopyranosyl-28-O-ß-D-glucopyranosyl-(1→6)-O-ß-D-glucopyranosyl-3ß-hydroxyolean-12-ene-28,29-dioic acid (1) from the fresh leaves, together with 11 known compounds, including six triterpenoid saponins (2-7), two caffeoylquinic acid derivatives (8-9), and three flavonoid glycosides (10-12). Their structures were determined on the basis of spectroscopic analysis and acidic hydrolysis. Compounds 3-5 and 8-12 were isolated from M. delavayi for the first time. Moreover, the known saponins 3-O-ß-D-xylopyranosyl-3ß-hydroxyolean-12-ene-28,29-dioic acid (3) and yiyeliangwanoside IV (5) exhibited protective effects on HepG2 cells damaged by the alcohol intakes, at a concentration of 1.0 µg/mL. The results indicated M. delavayi is an ideal dietary vegetable and herbal tea with potential hepatoprotective activity.[Formula: see text].


Assuntos
Araliaceae/química , Folhas de Planta/química , Substâncias Protetoras/isolamento & purificação , Saponinas/isolamento & purificação , Triterpenos/isolamento & purificação , China , Glicosídeos/análise , Células Hep G2/efeitos dos fármacos , Humanos , Estrutura Molecular , Extratos Vegetais/química , Substâncias Protetoras/química , Substâncias Protetoras/farmacologia , Saponinas/química , Saponinas/farmacologia , Triterpenos/análise , Triterpenos/química , Triterpenos/farmacologia
15.
Nat Prod Bioprospect ; 9(6): 357-392, 2019 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-31696441

RESUMO

Terminalia Linn, a genus of mostly medium or large trees in the family Combretaceae with about 250 species in the world, is distributed mainly in southern Asia, Himalayas, Madagascar, Australia, and the tropical and subtropical regions of Africa. Many species are used widely in many traditional medicinal systems, e.g., traditional Chinese medicine, Tibetan medicine, and Indian Ayurvedic medicine practices. So far, about 39 species have been phytochemically studied, which led to the identification of 368 compounds, including terpenoids, tannins, flavonoids, phenylpropanoids, simple phenolics and so on. Some of the isolates showed various bioactivities, in vitro or in vivo, such as antitumor, anti HIV-1, antifungal, antimicrobial, antimalarial, antioxidant, diarrhea and analgesic. This review covers research articles from 1934 to 2018, retrieved from SciFinder, Wikipedia, Google Scholar, Chinese Knowledge Network and Baidu Scholar by using "Terminalia" as the search term ("all fields") with no specific time frame setting for the search. Thirty-nine important medicinal and edible Terminalia species were selected and summarized on their geographical distribution, traditional uses, phytochemistry and related pharmacological activities.

16.
World J Microbiol Biotechnol ; 35(7): 113, 2019 Jul 09.
Artigo em Inglês | MEDLINE | ID: mdl-31289918

RESUMO

Camellia taliensis (W. W. Smith) Melchior is a wild tea plant endemic from the west and southwest of Yunnan province of China to the north of Myanmar and is used commonly to produce tea by the local people of its growing areas. Its chemical constituents are closely related to those of C. sinensis var. assamica, a widely cultivated tea plant. In this study, the α diversity and phylogeny of endophytic fungi in the branches of C. taliensis were explored for the first time. A total of 160 fungal strains were obtained and grouped into 42 species from 29 genera, which were identified based on rDNA internal transcribed spacer sequence analysis. Diversity analysis showed that the endophytic fungal community of the branches of C. taliensis had high species richness S (42), Margalef index D' (8.0785), Shannon-Wiener index H' (2.8494), Simpson diversity index DS (0.8891), PIE index (0.8947) and evenness Pielou index J (0.7623) but a low dominant index λ (0.1109). By contrast, that in the branches of C. taliensis had abundant species and high species evenness. Diaporthe tectonigena, Acrocalymma sp. and Colletotrichum magnisporum were the dominant endophytic fungi. The phylogenetic tree was established by maximum parsimony analysis, and the 11 orders observed for endophytic fungi belonging to Ascomycota and Basidiomycota were grouped into 4 classes.


Assuntos
Camellia/microbiologia , Endófitos/classificação , Endófitos/isolamento & purificação , Fungos/classificação , Fungos/isolamento & purificação , Filogenia , Chá , Ascomicetos/classificação , Ascomicetos/genética , Ascomicetos/isolamento & purificação , Basidiomycota/classificação , Basidiomycota/genética , Basidiomycota/isolamento & purificação , Biodiversidade , China , Análise por Conglomerados , DNA Ribossômico/genética , Endófitos/genética , Fungos/genética , Mianmar , Análise de Sequência
17.
Nat Prod Bioprospect ; 9(4): 287-295, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-31124011

RESUMO

Four new protopanaxatriol-type triterpenes (1-2) and glucosides (3-4), were isolated from the rot roots of Panax notoginseng (Burk.) Chen, along with four known ones (5-8). Their structures were elucidated on the basis of extensive spectroscopic analysis (HRESIMS, NMR, UV, IR, and OR) and acidic hydrolysis. The possible transformation pathway of these compounds were also speculated from ginsenoside Rg1. Compound 1, with a unique α,ß-unsaturated ketene in its side chain, showed significant inhibitory effects against NO production on Murine macrophage cells (IC50 = 4.12 ± 0.20 µM) and comparable cytotoxicities against five human cancer cell lines (myeloid leukemia HL-60, lung cancer A-549 cells, hepatocellular carcinoma SMMC7721, breast cancer MCF-7, and colon cancer SW480) to positive control, cisplatin (DDP).

18.
Fitoterapia ; 137: 104151, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-30999024

RESUMO

The norbisabolane-type sesquiterpenoids bearing a spiroketal functionality have been found in Phyllanthus spp. and showed anti-HBV activities. As part of an ongoing effort to search for promising anti-HBV sesquiterpenes from Phyllanthus plants, we report four new norbisabolane-type sesquiterpenoids, phyacidusin A (1), phyacidusin B (2), phllanthacidoid A1 (3) and phllanthacidoid N1 (4), from stem of P. acidus collected in Xishuangbanna, Yunnan province, China. The absolute configuration of new compounds was established by coupling constants and ROESY correlations, as well as comparation of NMR data with those of known compounds. The absolute configuration of new compounds 1 and 2 was further confirmed by X-ray diffraction. Compound 2 showed effect to HBsAg with an IC50 value of 11.2 ±â€¯0.01 µM, while compound 3 inhibited HBeAg secretion with an IC50 value of 57.1 ±â€¯0.02 µM. The results enriched the diversity of anti-HBV norbisabolane sesquiterpenes.


Assuntos
Antivirais/farmacologia , Vírus da Hepatite B/efeitos dos fármacos , Phyllanthus/química , Sesquiterpenos/farmacologia , Antivirais/isolamento & purificação , China , Células Hep G2 , Humanos , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Caules de Planta/química , Sesquiterpenos/isolamento & purificação
19.
J Agric Food Chem ; 67(19): 5318-5349, 2019 May 15.
Artigo em Inglês | MEDLINE | ID: mdl-30449099

RESUMO

Tea, as one of the most popular beverages with various bioactivities, is commonly produced from the fresh leaves of two widely cultivated tea plants, Camellia sinensis and C. sinensis var. assamica. Both plants belong to the genus Camellia section Thea, which was considered to have 12 species and 6 varieties according to Min's taxonomic system. Most species, except the cultivated species, are known as wild tea plants and have been exploited and utilized to produce tea by the local people of its growing areas. Thus far, six species and varieties have been phytochemically studied, leading to the identification of 398 compounds, including hydrolyzable tannins, flavan-3-ols, flavonoids, terpenoids, alkaloids, and other phenolic and related compounds. Various beneficial health effects were reported for tea and its components, involving antioxidant, antitumor, antimutagenic, antidiabetic, hypolipidemic, anti-inflammatory, antimicrobial, antiviral, antifungal, neuroprotective, hepatoprotective, etc. In this review, the geographical distribution of tea plants and the chemical constituents (1-398) reported from the genus Camellia section Thea and some tea products (green, black, oolong, and pu-erh tea) that have ever been studied between 1970 and 2018 have been summarized, taking species as the main hint, and the main biological activities are also discussed.


Assuntos
Camellia sinensis/química , Chá/química , Camellia sinensis/classificação , Camellia sinensis/crescimento & desenvolvimento , Humanos , Estrutura Molecular , Extratos Vegetais/química , Folhas de Planta/química , Folhas de Planta/crescimento & desenvolvimento
20.
Nat Prod Res ; 33(9): 1284-1291, 2019 May.
Artigo em Inglês | MEDLINE | ID: mdl-29745730

RESUMO

Two new sphingofungins G (1) and H (2) with a five-membered lactone ring were identified from the solid-state fermentation of Aspergillus penicilliodes Speg., a dominant microorganism isolated previously from the post-fermentation of ripe Pu-er tea, together with six known metabolites. Their structures were elucidated by extensive spectroscopic methods. All of them were isolated from the mycelia culture of A. penicilliodes for the first time. The known compound, trypacidin, exhibited potent cytotoxities against five human cancer cell lines, e.g. myeloid leukemia HL-60, lung cancer A-549, hepatocellular carcinoma SMMC7721, breast cancer MCF-7, and colon cancer SW480, with IC50 values of 0.55, 11.45, 10.95, 3.58, and 3.49 µM, resp., while cisplatin as the positive control, with IC50 values of 8.63, 24.15, 21.99, 27.29, and 23.61 µM, resp.


Assuntos
Aspergillus/metabolismo , Lactonas/isolamento & purificação , Linhagem Celular Tumoral , Fermentação , Humanos , Lactonas/química
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